Gilmore Girls fans longed to see Lorelai, Rory, and the town of Stars Hollow back on their TV screens again in Gilmore Girls: A Year in the Life, as well as hear what was always supposed to be show creator Amy Sherman-Palladino's famous final four words of the series. But then there was also the matter of Rory's boyfriends — who would she finally pick and stay with? MAJOR FINALE SPOILERS are ahead for Gilmore Girls: A Year in the Life. Rory actually doesn't end up with any of them, but she is pregnant, presumably with Logan's baby. But could Rory and Jess still end up together on Gilmore Girls ? Definitely.
Throughout the revival series, Rory spends a good amount of time back with Logan in a no-strings-attached relationship in London, even though he's engaged to marry a French heiress named Odette. In "Summer," Rory returns to Stars Hollow once some of her career prospects fall apart and she becomes editor of the Stars Hollow Gazette, where she gets a visit from the one and only Jess Mariano, who looks as good and is as sharp as ever. They drink bourbon during the day and he inspires her to write a book about the relationship between herself and Lorelai.
In "Fall," Rory excitedly tells Jess that she drafted the first few chapters of the book, but Jess tells Luke it's over, even though Jess looks lovingly at Rory through the window before he leaves. Let's face it, it's not over yet — even with a baby in the mix now. The revival drew parallels to Lorelai and Rory's relationships all over the place. Logan is clearly her Christopher, the guy she can't seem to quit and has a lot of bad timing with. That leaves Jess to be her Luke, the guy who is always there for her when she needs him — and that was very clear from his appearance in Gilmore Girls: A Year in the Life.
But the most telling moment in Jess' favor doesn't even include Jess — it's a scene with Rory and Christopher in "Fall." Rory visits her father for what seems like book research and tells her that their mother-child bond was the strongest. "It was in the cards," he tells her. "Lorelai and you, from the first moment I saw you two together, no one was getting between you guys." That could very well be the same for Rory and her child, with even the father of the baby (probably Logan) getting in the way of her mother/child bond.
Rory is not the type of person to marry someone just because she's pregnant, and she's said her goodbyes to Logan (and to Dean for that matter). The only person she really seems to have unfinished business with is Jess. Coincidentally, he's also the only ex of hers who is not in a relationship, which makes the odds much higher that they end up together. As frustrating as it is that the series ended on a cliffhanger, I feel in my heart that Rory and Jess aren't done. They'll end up toegether some day — just like Luke and Lorelai.
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